Posted October 14, 2025 by

Over the past few months I’ve attended a few author dinners in NYC. This is where a group of authors/prospective authors get together and discuss whatever is concerning them. There might be a debate around the future of writing and the impact of AI. We might argue about traditional publishing versus self-publishing. And so forth.

Almost all of the authors/prospective authors aren’t in the personal finance space, and they tend to be older and far more successful than I am. I don’t say this to downplay anything I’ve done, but to emphasize that there’s a difference between selling thousands of books and selling millions.

The thing that really surprises me though is how they think about money. At some point during the conversation, the discussion inevitably turns to personal finance. And when it does, it’s always an eye-opener.

For example, one online creator complained about the price of beer at their local brewery. It was $15 after tax and tip. I get it. A beer should feel cheaper than $15, even at a craft brewery. But this complaint is coming from someone who posts about the millions they’ve made online.

While I don’t know their exact financial situation, based on their public earnings alone they are either deep in Level 4 ($1M-$10M) or low Level 5 ($10M-$100M) in their early 40s. This would put them in the top 1% of U.S. households for their age, yet they are complaining about paying $5 extra for a beer.

Their cognitive dissonance is one of the most fascinating things in the world to me. How can you be so wealthy and care about something so insignificant to your finances? You’re complaining about the beer, yet you can buy the brewery.

You might argue that such complaints are just performative or are used as a way to connect, but I don’t think that’s the case. Such spending gripes typically occur unprompted and are always about individual expenses, not the price level in general or how these prices could impact others.

But spending issues are just the tip of the iceberg. I also get a sense of financial insecurity from some of these people who should have nothing to worry about. People in Level 5 ($10M-$100M) who are concerned about the success of their next project. People in the 1% who still seem dissatisfied. And if they are dissatisfied, then how should I feel? It reminds me of that Chris Rock joke:

If Bill Gates woke up with Oprah’s money, he’d jump out the window.

Would you be content as Oprah in this scenario? I would. However, some people wouldn’t. The core issue is that wealth is almost always judged on a relative basis, even when it shouldn’t be. Alain de Botton summarized this beautifully in Status Anxiety:

Wealth is not an absolute. It is relative to desire. Every time we yearn for something we cannot afford, we grow poorer, whatever our resources. And every time we feel satisfied with what we have, we can be counted as rich, however little we may actually possess.

The bigger problem is when people yearn for things that they imagine they need. They can then justify their behavior to acquire more money, even when that won’t ultimately solve their problems. The more successful people I’ve met, the more I’ve realized this to be true. Financial security isn’t what they’re chasing (even if they say otherwise). It’s something deeper.

Where does it come from? I’m not sure, but Tiffany “The Budgetnista” Aliche once said, “Ambition is a trauma response.” Her argument was that many of the most successful people weren’t driven by money, but as a reaction to something that happened in their past. While this isn’t true for every ambitious person, there are plenty of examples where it holds.

Michael Jordan was known for being driven by insults from his competitors, to the point of making them up. Lady Gaga used the pain of sexual assault and being bullied in school to fuel her music. Steve Jobs was fired from Apple in 1985 and built NeXT, which was acquired by Apple in 1996, eventually leading to Apple’s resurgence.

There’s a drive inside many successful people that goes beyond money and logic. People who keep going at 100 miles per hour even when they don’t need to. More partnerships. More deals. More speaking gigs. More books. It seems never-ending.

Money is a convenient excuse for such behavior because who would say no to more money? But it’s not the real reason. 

I raise these issues not to judge my fellow authors, but to illustrate the very human side of money, the behavioral side of money. Though I can look at money in this cold, calculating fashion (given how much time I’ve spent studying it), I know others can’t. They experience sticker shock regardless of what’s in their bank account. They can feel insecure no matter what my financial calculator tells them.

Similarly, I know that I behave in certain ways that experts in other domains would think are bizarre. I probably “complain about $15 beers” with regards to my health, relationships, and career all the time without realizing it.

Nevertheless, I know that it takes more than numbers to help people feel differently about their money. I can show you why you can use the 5% Rule or why you should make a lump sum investment, but I know that you probably won’t follow either.

Despite my bias toward data, the solutions to some of your money problems won’t be found in a spreadsheet. I know this, but it’s still hard to ignore the numbers. Because there’s a disconnect between what’s going on in the world and how we feel about it. We are living through the richest period in human history, but you’d never know it by talking to many of us. We have all the money and none of the satisfaction.

Thank you for reading.

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This is post 472. Any code I have related to this post can be found here with the same numbering: https://github.com/nmaggiulli/of-dollars-and-data